4.7 Article

3,6-Dioxaoctamethylenediamminium trifluoromethanesulfonate [3,6-DOMDA]OTf as a novel ionic liquid catalyst for the synthesis of functionalized 1,4-dihydropyridines

Journal

JOURNAL OF MOLECULAR LIQUIDS
Volume 232, Issue -, Pages 174-181

Publisher

ELSEVIER
DOI: 10.1016/j.molliq.2017.02.073

Keywords

3,6-Dioxaoctamethylenediamminium trifluoromethanesulfonate[3,6-DOMDA]OTf Functionalized 1,4-dihydropyridines; Catalysis; Ionic liquid; Solvent-free condition

Funding

  1. Bu-Ali Sina University
  2. Iran National Science Foundation (INSF) [95831207]

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In this research [3,6-DOMDA]OTf as a novel ionic liquid was synthesized and fully characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (H-1 NMR, C-13 NMR, F-19 NMR), Mass spectrometry, Thermal gravimetric (TG), Derivative thermal gravimetric (DTG) and Differential thermal analysis (DTA). Described [3,6-DOMDA]OTf was used as a novel ionic liquid catalyst for the domino one-pot four-component synthesis of functionalized 1,4-dihydropyridine derivatives by a combination of various aldehydes, malononitrile, acetylenedicarboxylates and anilines under solvent-free condition at 50 degrees C. [3,6-DOMDA]OTf catalyst with etheric bonds can be recovered and reused up to six times without significant loss of activity. The mentioned compounds were synthesized in high to excellent yields, short reaction time and their products could be easily separated. (C) 2017 Elsevier B.V. All rights reserved.

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